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Citation: GUO Wenyan, CHEN Jianxin. A New Method for Synthesizing α-Aminoamide Compounds[J]. Chinese Journal of Applied Chemistry, ;2013, 30(10): 1114-1119. doi: 10.3724/SP.J.1095.2013.20600 shu

A New Method for Synthesizing α-Aminoamide Compounds

GUO Wenyan ^a,b, ,
CHEN Jianxin ^a

a. College of Chemistry and Material Science, Shanxi Normal University, Linfen 041004, China;
b. Modern College of Arts and Science, Shanxi Normal University, Linfen 041000, China

Received Date: 24 December 2012
Revised Date: 24 February 2013

It was found that boron trifluoride etherate was an effective catalyst for the reactions between carbamoylsilane and imines. The influences of various substitution groups(ethyl,isopropyl,trifluoromethyl,styryl,phenyl,furyl,thienyl,pyridyl) on the C-terminus of the parent iminium to the reaction have been studied and some α-aminoamides were synthesized. The stereoselectivety of the reaction was found by connecting chiral alkyl(S-1-phenylethyl) on the N-terminus of the iminium and the highly stereoselective product was obtained (diastereomer ratio of 14:1) by connecting chiral alkyl both on the N-terminus of the iminium structure(S-1-phenylethyl) and on the N-terminus of carbamoylsilane(R-1-phenylethyl). So this is a new method for stereoselectivly synthesizing α-aminoamides.
- imine,
- carbamoylsilane,
- α-aminoamide,
- asymmetric synthesis
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